You're A Heartbreaker
by Tarafina
Summary: /:AU – High School:/ Chloe Sullivan tries, and fails, to keep from falling for the charming ladies man Oliver Queen, who's out to win her affections.


**Title**: You're a heartbreaker (Don't you mess around with me)  
**Category**: Smallville  
**Genre**: Romance/Drama/Humor  
**Ship**: Chloe/Oliver  
**Rating**: Teen/PG-13  
**Word Count**: 3,802  
**Summary**: /AU – High School/ Chloe Sullivan tries, and fails, to keep from falling for the charming ladies man Oliver Queen, who's out to win her affections.

**_You're a heartbreaker (Don't you mess around with me)  
_**-1/1-

Chloe could see him coming out of the corner of her eye from where she stood at her locker, pretending to be completely distracted by the stack of articles in her hands that had yet to be fact- or spell checked; despite herself, she felt a smile tugging at her lips.

Oliver Queen, a senior at their high school and veritable ladies man, had his sights set on her. And while she outwardly showed disdain for his obvious display of interest, telling herself that she was just who he saw as his flavor of the month and she'd be discarded as quickly as she let her defenses down, she couldn't help but find him just a little bit handsome, and smart, and annoyingly charming.

"Chloe," he greeted, with that hint of knowing, as if he knew she was watching him as he approached. He leaned back against the bank of lockers next to hers, tugging the sleeves of his probably very expensive shirt up his arms. He even smelled expensive; the cologne he wore reached her nose and made her pulse speed up. Men shouldn't smell that good. Men that already looked as handsome as he did shouldn't smell that incredible. She would have to take it up as her next protest, because really, how was a girl supposed to focus on sniffing out the truth when they had a guy like him hanging around?

She stuffed her things back into her locker and closed it, sighing as she waited for his latest attempt at getting her to go out with him.

He tipped his head and eyed her, his mouth curved in an attractive grin that said he knew exactly how much he was affecting her. "So I was thinking... I'll borrow my dad's favorite Lamborghini, put in a take-out order from _L'oie D'or_'s and we can picnic down by the lake. If you get bored, I'll bring along my bow and arrow and show you why our archery club has so many trophies..." He wiggled his eyebrows at her.

Chloe scoffed, closing her locker door and turning to raise a brow at him. "Listen, Queen, I get that showing off usually gets you a free pass to half the school's female population, but I really don't care if you hit the bull's-eye or accidentally take one of your toes off..." She smirked at him. "But you have fun down at the lake tonight, big guy..." She patted his chest mockingly, faltering momentarily when her hand met solid muscle, and moved to walk past him.

"I'm not sure which part of that I should touch on first... That you think I'm a manwhore or that you think I'm just trying to show off..."

Chloe paused in her steps, turning her head to eye him skeptically over her shoulder. "Is this where you shock me with your depth of character?" she wondered, lip curled.

"Obviously not, since you don't think I have any," he muttered, his chin falling and his eyes hitting the ground.

For the first time in the last two weeks of Oliver trying to talk her into giving him the time of day, Chloe was seeing something other than the smug, rich boy he portrayed every moment of every school day. And while she didn't want to let herself be snared by the possible trap of a spider reeling in its prey, there was a part of her that felt bad for putting that disappointed look on his face.

Rolling her eyes to herself, she bit her lip and turned around, crossing her arms over her chest. "Oliver, you're the most popular guy in this school. There is _literally_ a club dedicated to admiring you, which is creepy and weird and, frankly, I've wondered how they worked it past the school board, but… The point is, you have your pick of every girl in the school; and from what I've heard, picking is a hobby of yours..." She stared at him seriously. "Despite how often my name gets splashed in the local newspaper because I chased the wrong story right into the bad guy's clutches, I'm just your average good girl. I'm not looking for Prince Charming to sweep me off my feet. I like them firmly planted on the ground, preferably in a comfortable pair of sneakers, so I can keep running toward that elusive dream of a Pulitzer. So you... Pulling your 'just give me a chance' routine, it's really not necessary. I'm sure you're a nice guy who would be a great date. And I'm sure, like every other girl who's ever met you, I'd be swept away by it if I let myself go there... But I don't _want_ to. I don't want to be another name on a long list of temporary arm-candy. So let's just put this to rest and you can move on to the next girl with her heart on her sleeve, all right?"

Okay, so maybe that wasn't as encouraging as she'd meant it to be. Originally, she thought maybe she'd soothe his broken ego and he'd be on his merry way. But she might have more or less insulted him, implied he might have the ability to make her fall in love with him, and then reiterated that he was a manwhore. God, she sucked at this!

She was much better behind a computer, where she could hit the backspace button whenever necessary and scrub out all of her stupid. Her talent laid in chasing down leads and writing interesting spins on the latest scandals of Star City. Not convincing boys she wasn't interested in their brand of romancing. And certainly not boys like Oliver Queen, who was captain of the lacrosse and archery teams while maintaining a 4.0 GPA, and still somehow managed to talk every attractive girl in the school to date him. Of course, it also didn't hurt that he was the progeny of two philanthropic billionaires.

"Wow, you are just not pulling any punches," he said, reaching up to rub a hand over the back of his neck, stretching his dark green shirt across his impressive chest.

Did she mention he was handsome? Because even that word felt lacking. He was tall and broad shouldered, with chiseled features and tanned skin. More than a few times Lois had convinced her to watch lacrosse practice after school and seeing Oliver without his shirt on had been… eye opening. But, while hormones usually drove the decisions of most of her peers, Chloe thought she was more level-headed than that. She wasn't going to let some boy derail her hard work just because he happened to have a six-pack and a devastating smile. She was stronger than that; she had more self-preservation than that, too. In his wake were a long string of broken hearts and Chloe wouldn't have hers added to the mix; no matter how genuine he might act.

"Look, I… I think we've got our wires crossed here," he said, motioning between them. "I get that my social standing in this school, with… with girls, it's kind of up and down." He frowned. "I was kind of hoping maybe you wouldn't be reading into the hype, since checking your sources is kind of standard with your future career choice, but hey, I get it, it's easier to assume that I'm the one breaking hearts all over the place than dig a little deeper…"

She scoffed at his obvious attack on her integrity, but before she could even argue his statement, he rushed to continue.

"Have I made a few bad choices? _Yeah_." He nodded. "After Tess and I broke up, I was an idiot. It was the first time I fell in love and I was scared. So when she dumped me for being such an ass, I started dating around… a _lot_. And maybe a few of those girls had feelings for me that I didn't reciprocate, but I never went out of my way to make anybody feel like that…" He shook his head. "So I have a reputation for breaking hearts, it's not something I was trying to do. Not that it really makes it any better, I guess..."

Okay, so maybe that might have, _possibly_, chipped away at her armor a tiny bit. If this was all an act, he needed to get himself into a drama class, because he was just Oscar material waiting to happen.

Licking his lips, Oliver dropped his eyes to the floor for a long second before finally taking a step closer to her and raising his gaze to meets hers. "I know you've got this image in your head of who I am. I know I'm just some rich jerk that you probably think catches all the breaks because my family has money and I'm not hard on the eyes…" He chanced a grin. "But I'm not asking you out so I can break your heart, Chloe. I'm asking you out because you're funny and smart and I read the newspaper every day because I know you wrote half the articles…" He reached up and brushed a hand through his hair. "And seeing your name makes me smile, because you're witty and a little crazy and you push the limits of your safety on a pretty regular basis, which is simultaneously scary and, being an adrenaline-junkie myself, kind of attractive…"

She snorted, rolling her eyes.

"I think you're beautiful, even when you're glaring at me for trying to ask you to the dance last week or when I offered to work on your paper or when you shot me down just because I tried to pick up the books you dropped yesterday…" His grin widened. "I like you, and I think you like me. Or you could…" He bit his lip and raised a brow. "So I'm gonna ask you again and you can tell me no if that's what you want. I can't guarantee I'll stop asking… In fact, I might have a banner in the works and possibly a plan to hijack the school's PA." His lips twitched with amusement as he added, "I'm also starting my own Chloe Sullivan Appreciation fanclub, since now I know I don't need the school board's approval, so I don't think you'll be getting rid of me anytime soon… Y'know, it's probably just smarter to give me a chance."

She laughed, fighting and failing to keep a smile from forming. "Sounds like you're a bit of a wordsmith yourself, Queen."

He raised an eyebrow, a devastating grin making her stomach flip-flop. "That mean you'll give me a chance?"

"That…" She bit her lip. "That means I'll reconsider you for a spot on the paper." She turned on her heel to leave, hips swaying.

"You know, if I'm on the paper we'll be spending a lot more time together…" he called after her, humor lacing his voice.

She chuckled to herself and turned around, walking backwards as she replied, "Ya don't say…"

He nodded, licking his lips. "I like a challenge."

She winked at him. "You got one."

With that, she turned back around and walked away, feeling pretty good about the whole thing.

Okay, so fine, maybe she wasn't as unique as she thought she was. Oliver Queen wanted a date and he had a rather charming way of getting one. Did she know for sure it wasn't an act? No. But, then, she was a sleuth extraordinaire, so… She might just have to do a little more snooping, check some sources, and really give all of her attention to the Boyfriend Material or Not debacle that was her current love life. Either way, she might have just filled a spot on the paper, and _hey_… He wasn't bad to look at. She decided to look at the situation optimistically and not focus on the fact that ten minutes ago her defenses had been impenetrable and now they were just short of being rubble.

Of course, living life dangerously was how things usually went for her, so maybe she should just strap in and let things happen as they should. If he managed to check out and really wanted to hop on her wagon of weird, then why not let herself get lost in it? At best, she got a cute boyfriend who could match her brains, drive, and possibly even join her on a few adrenaline fueled stakeouts. At worst, she went on a few dates, got dumped, and possibly, maybe, had her heartbroken. She wasn't sure which way the odds were leaning, but she was willing to find out. Maybe because he was cute, maybe because he seemed genuine, and maybe because, despite all that she learned and all the warnings she'd heard, she actually did like him. Whatever the reason, she had some time to figure out if it was what she wanted, and she was going to use it to her advantage. Starting at ground zero…

"Tess!"

The pretty red head turned to look at her, raised a brow, and smirked coldly. "Sullivan… Didn't know the vice principal let you out to play without a chaperone any more."

"He doesn't." She grinned. "I lost him somewhere around the chemistry hall."

She laughed shortly. "Well? What do you need? A sound bite for your paper, or some better advice on how not to get caught when you're attempting to tail a crooked senator?"

"Appreciate you looking out for my well-being and all, but this is something a little less Nancy Drew and a little more Oprah…"

Tess' lips pursed in a frown as she crossed her arms over her chest. "All right, I'm listening…"

"Oliver," she said simply.

The red head's gaze fell and her expression went blank. "Go on."

Chloe stared at her. "On a scale of Jimmy Carter to Bill Clinton, is he the guy you trust or the guy who lies to your face?"

She took a long moment to answer, casting her gaze away, her expression guarded. Finally, she cracked a mocking smile. "Don't tell me you're falling for that old game too?" She closed her locker and hiked her bag on her shoulder. "Despite your pathetic record of getting caught and playing damsel in distress, I thought you were one of the few smart ones around here…"

Rolling her eyes, she dismissed the dig. "Look, I know the record. The number of pining ex's he's racked up isn't exactly encouraging. But I'm not talking to the Flavor of the Week; I'm asking his one major girlfriend if he's worth the risk…" She shrugged. "Admittedly, there's still a good chance you either love him or hate him too much to be objective, but I guess I'm hoping you're a little more Jimmy Carter too."

Tess stared at her thoughtfully before finally giving a quick nod. "Look, Oliver is…" She sighed. "He's good. Underneath all of the bravado, he's a good guy. Maybe he wasn't all in when we were together. Personally, I think being together, getting too close, it spooked him. He couldn't control it so he screwed it up."

Chloe nodded slowly, frowning.

"He needs someone who's patient… Someone who can keep up, doesn't get clingy, and who isn't easily distracted by all the surface stuff… Because if it's just about money or image or the shiny car he drives, he'll lose interest quick." She stared at her seriously. "He needs substance, he deserves it, and he knows it. He might play the unaffected, throw around your money, pretty boy thing up, but it's not who he is."

"Okay," she said, taking a few steps back. "Thanks for the tip."

As she turned to leave, however, Tess called after her. "Hey…"

She looked back.

"He's more Carter than Clinton…" Tess tightened her crossed arms. "And when he loves, he does it with all of himself."

She offered a faint smile before walking away, trying to absorb what she'd learned.

Chloe spent most of her afternoon distracted. She'd been trying so hard for the last two weeks not to look past the general package Oliver presented of a spoiled rich boy out for kicks. But now that she had a little more insight not only from him but his ex, she was starting to get far too involved. He wanted a date and he seemed to think it could go somewhere. He was trying really hard not only to impress her but to find ways for them to connect. The gifts and showing off wasn't working, so he tried joining the paper and being chivalrous by opening doors and carrying books. No matter how much she snapped at him that she didn't need his help, he was there, trying. And it wasn't in a creepy, unnecessary, invade her space kind of way, so much as a… Hey, I like you, and I think you could like me too if you give me a try, kind of way. Which she had tried really hard to pretend was not as genuine as it seemed to be. But it looked maybe she was wrong.

A knock at her office door drew her attention and Chloe raised her head from where she'd been staring at her computer screen, the words long blurred together as she'd given up trying to edit one of her grunts columns and instead focused on her own personal issues. She blinked twice when she found Oliver standing in the doorway.

"Did you book an appointment that I missed?" she asked, leaning back in her chair, a smile tilting her lips.

Without missing a beat, he said, "Well, I checked in with your secretary, Madame Editor, but he said getting a chance to talk to you probably wasn't in the cards."

"So you took your own initiative I see…"

He walked into the room, clasping his arms behind his back. "Well…" He shrugged. "I thought it might reflect better if I showed off how equally persistent I can be." He took a seat on the corner of her desk and grabbed up the stress ball she'd been given by Lois. He squeezed it a few times absently, gazing around her office, the walls covered in old articles, some for the high school paper, others from the local newspaper exulting her prowess for getting into sticky situations.

"You don't do much by the book, do you?" he asked, staring at the cut out of her having a stare-down with a big wig attorney she'd had arrested for racketeering.

"There are too many things going wrong and too many questions that need answers for me to just follow the status quo…"

He nodded. "So you like it when things get exciting? When good triumphs over evil, the little guy comes out on the winning end, your own David versus Goliath showdown…"

"Only with less decapitation, preferably."

His lips twitched and he turned to look at her. "You're not like most girls."

She laughed, ignoring the way she knew her cheeks had flushed pink. "Does that line work often?"

"Yes…" He grinned. "But it's not usually true."

Her eyes narrowed as she stared back at him. "So… You here for a spot on the paper?"

He shook his head. "I'll take one if you've got one though."

Her eyebrow arched. "What do you want, Oliver?"

"Direct... I like that."

"You seem to like a lot of things."

"About you, sure."

She waited, watching him as he continued to squeeze the stress ball.

Finally, he cracked. "No Lamborghini, no expensive dinner, no showing off at all… I won't even bring my bow!" He held his hands up to show how honest he was being. He stared down at her, brows hiked. "We'll get ice cream, take a walk in the park, and we'll… _talk_. Get to know each other." He grinned. "You can tell me some of your increasingly bizarre cases…" He pointed a thumb back at the Wall of Weird she kept.

She hummed to herself, chewed her lip, and finally… "Okay."

He blinked. "Okay?" He perked up and then smiled. "Okay." He hopped off her desk, tossing her stress ball back to her, winking as she caught it easily. "Pick you up at six?"

"How about I meet you at the ice cream vendor in Star Park?" She nodded her head back to the computer. "I can finish up here and then drive over."

He grinned, nodding. "I'll see you there." He walked toward the door, pausing to look back at her. "So, what did it? What made you change your mind?"

"A little of Jimmy Carter," she mused. "But mostly… I make you nervous."

His brows furrowed, lips opening as he drew in a deep breath, but had no words to answer with.

She grinned and tossed the stress ball in the air. "Six o'clock," she told him.

"Right." He backed toward the door, still a little confused, but mostly just glad with the outcome. "Don't work yourself too hard, Sullivan… I'll take it personally if you're late."

With a laugh, she waved him off. "If you get there first, I'll take a waffle cone with one scoop of anything coffee flavored."

"Got it."

As he walked out the door, Chloe turned back to her computer and grinned.

Maybe the date would be a disaster, maybe the whole thing would all blow up in her face, or maybe they'd click. She'd just have to find out for herself.

Two hours later, Chloe found a grinning Oliver holding two ice cream cones, one coffee bean blast and one mint chocolate chip. She was five minutes early, he was a little eager, and she took it for the good sign it was.

Chloe could be patient; she had to be with the amount of stakeouts she'd been on. She didn't care about the material world Oliver lived in or what he could offer her because of his social status. What she did like was that he was sarcastic and smart and he listened when she talked, he encouraged her to tell her more about the weird things she'd seen and the bad people she'd helped take down. She felt equal to him, regardless of whether he was popular or a billionaire or anything else that might divide them. And when the date ended, she knew that his fingertips were callused from his bow and arrow, she felt them swipe across her cheek to tuck her hair away. She knew his eyes were an incredibly warm shade of brown, darker than usual just before they kissed. And that he tasted like mint, although she thought that was probably more the ice cream than anything.

She also knew that getting her heartbroken might just be worth it, but she didn't really have to worry about that.

**[End.]**

* * *

**Author's Note**: _So, recently, my laptop was stolen. CURSE YOU, THIEF, TO THE DEPTHS OF HELL! RRRAAAAWWWRRR! *clears throat* Anyway… I've returned to my old PC which wasn't getting much love. And since it was running kind of slow, I decided to go through some of my old stories, see what I'd get rid of since I was sure I had a ton of half-finished, never-to-be-continued stories that I could wipe out when I stumbled upon this. Also only half-finished, but since I was inspired, I finished it. I know I don't write Chlollie often any more, and I have far too many fics of these two that have yet to be finished, and certainly deserve to be, but here ya go anyway. I don't know when my muse will return on a regular basis. I'm currently spending most of my time in college, so time for writing and a cooperative muse are difficult to wrangle. I hope you enjoyed this all the same! ^_^_


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